


Every Trousseau Needs a Corset

by LikeBetteOnABadDay



Series: Every Trousseau Needs a Corset [1]
Category: Teen Wolf (TV)
Genre: Alpha/Beta/Omega Dynamics, Alternate Universe, Alternate Universe - Historical, Bad Dirty Talk, Bondage, Consent Issues, Forced Crossdressing, Forced Feminization, Gags, Genderplay, Humiliation, Lol what is this even, M/M, Plot What Plot/Porn Without Plot, Rape/Non-con Elements, References to Bestiality, Rimming, Rope Bondage, Sex Toys, Spanking, Verbal Abuse, Verbal Humiliation
Language: English
Status: Completed
Published: 2013-08-20
Updated: 2014-07-25
Packaged: 2017-12-24 03:02:47
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 13
Words: 12,908
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/934523
Author URL: https://archiveofourown.org/users/LikeBetteOnABadDay/pseuds/LikeBetteOnABadDay
Summary: <blockquote class="userstuff">
              <p>Derek Hale and his boy bride. 'Nuff said.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> This is a kink-fic. Please, please do not leave me messages saying you are triggered by the content, or that I should tag this better; there are already multiple tags for the content, and I believe that they suffice. If you think you might be triggered by reading a kink with multiple kinks, please don't read it. Thank you for your consideration.

Derek went himself to receive his bride at the train station. As head alpha of all the seven packs that dwelt in the town of Chastity, Pennsylvania, he could have ordered any of his men to meet the train, but this was tradition. Derek may have been the youngest head alpha in three centuries, but he'd been brought up to respect rituals.

Steam billowed from the train as it pulled into the station. Derek stood at attention, an assistant on either side. Chastity rarely received many visitors, and he wasn't surprised when no one got off the coaches meant for the passengers. He was more interested in the luggage coach, anyway.

Two uniformed men slid open the door of the luggage coach from the inside. Despite his calm demeanor, Derek's cock twitched with interest as he saw the large wooden crate nestled among the hay in the coach. He'd specifically requested the hay himself, so that his fragile property wouldn't be damaged along the way. He made a mental note to tip the guards extra.

The crate was carefully lowered to the platform. With an elegant flick of his head, Derek gestured to his men to get the box open. They moved forward quickly and silently, and within a minute, the strong cables binding the crate had fallen away, and the lid was being opened with a creak.

Derek took a single, measured step ahead. He glanced down perfunctorily into the crate, then nodded and held his hand out for the clipboard that one of the guards was holding. 

A glance had been enough to confirm that the merchandise had arrived safely. The other reason Derek hadn't dared to dwell on the contents of the crate was that he hadn't been sure he'd be able to keep his hands from straying into the box if he'd allowed himself to feast his eyes for one more moment on the gorgeous creature inside.

Within the crate, Stiles Stilinski lay curled in a ball, embedded snugly into the surrounding hay. His slender, sixteen-year-old body was dressed in a gown of soft, see-through gossamer. Tight ropes encased him from head to toe. The bindings held his wrists together in the small of his back, and also wound around his elbows so tightly that they almost touched. More coils of rope were wrapped snugly around his ankles, and both above and below his knees. His gown was stretched tightly across his chest, revealing the small hoops that his tits had been pierced with. As requested, he wore nothing beneath the gown, and Derek was pleased to note that the boy's cocklet and ball sac were bound securely, if crudely, with what appeared to be thick twine. 

Before he signed the receipt, Derek swiftly pushed the boy onto his side to inspect his bottom. Although covered by his soft pink gown, the round globes of his buttocks were clearly visible through the sheer fabric, which was somewhat stained along his crack with the oils that had been used to prepare him. From between those plump, alluring cheeks protruded the rounded base of what Derek knew would be a long wooden phallus that had been deeply inserted into the boy's hole. Ingeniously, the rope around his soon-to-be-bride's wrists had been attached to another short length that was bound securely around the base of the toy, and that disappeared between his legs, presumably also attached to the bindings around his genitals. Any attempt to struggle free of the ropes would essentially have led to the boy fucking himself on the phallus, as well as tugging on the bindings around his sex. As if exhausted from said struggles, the boy was soundly asleep, drool leaking from the ring gag keeping his mouth open.

Derek signed the form with a flourish. _Received in good condition._ Then he gestured to his men to close the crate and stow it in the back of the truck.

 _Welcome to your new home, my bride._

 

tbc


	2. Chapter 2

**Notes for the Chapter:**

> TY for the fb so far. Y'all are fine. :)

As the truck rattled its way down the dusty streets back to Hale Manor, Derek pulled out the envelope that had been handed to him along with his merchandise. It was a slim sheath of cream-colored paper, sealed with a simple red circle of wax. The letter inside was short and to the point, as he'd expected.

_Alpha,_

_I hope all the arrangements were to your liking. I did my best to ensure that your orders were followed to the letter._

Derek smiled at the sight of the neat signature at the bottom.

A few minutes into the journey, muffled moans could be heard from the back of the truck. "Stop!" Derek commanded, and the vehicle lurched to a halt by the side of the road. In a few terse words, he ordered that his fiancée be brought out of the crate and placed in the seat next to him. The sweet perfume of Stiles's body greeted Derek as soon as the crate was reopened, and he rubbed his palm over the burgeoning swell in his trousers. He would not break ritual and penetrate his wife before the mating ceremony, but the rules didn't say that they couldn't find pleasure in each other before they were officially mated.

The pliant, erotically-clad body was lifted carefully into the seat beside Derek, and he bit back a groan at the sight of the tight bondage, still secure around his mate. Whatever drug Stiles had been given was clearly still in his system; he could barely manage more than a few weak wriggles, his head lolling on the seat and inadvertently coming to rest on Derek's shoulder.

"There, my sweet," Derek murmured, sliding an arm around the boy and nuzzling into his soft hair. He brought up his other hand to softly touch the gagged mouth, tracing the drool-wet, held-open lips with a fingertip. "God, your mouth." Tilting his boy's head back, Derek slipped his tongue out and stole a parody of a kiss, letting himself explore the omega's sweet-tasting mouth with leisure. The boy couldn't really kiss back with his lips stretched into a wide 'O', but no matter. There would be time enough for more participatory kisses in the future. As he toyed with the omega's tongue and licked into the hot little hole of his mouth, Derek let his hands wander the boy's body, molesting the bound, silk-clad limbs. One hand cupped the perfect bottom, squeezing against the wood impaling the omega's hole and making the creature whimper deliciously. Derek let out a groan of his own, tonguing the boy's mouth more hungrily. "If we keep this up," he growled between kisses, his other hand groping blindly for the boy's chest and squeezing a pierced tit with fervor, "I won't be able to help myself."

Abandoning the molested tit, he let his hand wander lower, past the omega's belly, slick with sweat and quivering with his weak, struggling breaths. When his hand located its prize, the boy arched up involuntarily, pushing his bound sex up into Derek's palm. "Fuck, my needy little slut." Derek squeezed his handful gently, letting his thumb glide across the soft, wet tip of the boy's captive cock. "Love that clit all swollen and wet for me." 

He continued his molestations over the hour-long drive, reveling in the soft moans and whimpers of his barely-awake omega.


	3. Chapter 3

**Notes for the Chapter:**

> Warning: references to bestiality.

The drive ended all too soon for Derek’s liking. He’d spent the last twenty minutes or so biting and suckling wantonly on the omega’s nipples through the dress, and the barely-there material was soaked with his saliva, revealing hardened little nubs surrounded by flushed, well-marked skin. As the vehicle pulled into the long, tree-lined driveway of Hale Manor, he pulled his mouth off the boy’s tit with a last suck and a reluctant sigh. His own lips were swollen and wet with all the kissing and biting they’d done, and he pulled a pristine white handkerchief from his pocket to pat them dry. Almost as an afterthought, he balled up the material and stuffed it into the omega’s mouth, relishing the sight of his well-gagged mate and the way the cloth gag muffled his already faint moans.

“I must attend to business,” Derek said, leaning over his captive mate for one last, long lick up the side of his face. “I’ll see you later, my little slut. Don’t worry. You shall be well-pleasured in the meantime.”

The omega whimpered, his eyes going wide. Chuckling, Derek bit his ear fondly and headed into the house.

*

The afternoon passed in a blur of activity; a head alpha’s work was truly never done. Given his station, Derek had set up a home office that was separate from the private study in which he liked to relax.

Aside from the mansion itself, the grounds also consisted of elegant stables as well as several barns with well-groomed oxen, pigs and sheep, and kennels with Derek’s prized pack of dogs. While it was against the law to breed omegas with animals without the express permission of both alpha and omega, Derek had allowed himself several indulgent fantasies about the ways in which the stables and barns could be put to highly pleasurable use. 

As the day slipped into early evening, Derek’s restlessness—and arousal—would no longer be denied. Wrapping up the day’s affairs an hour earlier than his usual time, he got to his feet and headed to the basement, which had been converted into a well-stocked room where his lovely bride was to be groomed, beautified and pleasured in the days before the mating ceremony. It would have been entirely inappropriate, of course, for the omega to share his alpha’s chambers before they were legally wed.


	4. Chapter 4

The renovated basement was large and well-furnished. One of the reasons Derek had chosen this particular room to cater to his omega’s needs was that it was the only room in the manor, barring the enormous ballroom, that had the space for all the required furniture. The ballroom was too public for the intimate grooming sessions that Derek had organized, but it would serve well to host the post-wedding festivities, when the new bride’s considerable charms would be exhibited to every guest.

The well-stocked basement also afforded Derek and his boy the privacy they would require for their lovemaking over the next few days. The omega would be moved to Derek’s own chambers after the mating ceremony, of course, but until then, they would need a space that would allow them to continue with their excursions of intimacy for prolonged durations without being disturbed. Almost half the room was taken up by a large four-poster bed: not as lavish as their marital bed would be, but large enough for at least three or four of Derek’s men to lie with the omega and pleasure him with their mouths, seeing to the boy’s needs while Derek was attending to business.

Even before Derek stepped into the room, the heady fragrance of desperately-aroused omega hit his nostrils. The sight that greeted him when he pushed the door open was even more delicious. 

According to Derek’s instructions, the omega’s travel-stained dress had been removed, and his body cleansed with perfumed lotions and oils. It gleamed under the soft lighting, golden skin begging to be licked and stroked and marked. He was dressed for bed already, wearing a tiny silk negligee, pure white and bordered with exquisite lacework. The nightgown ended just below his waist, leaving his rump bare and inviting. He was bound in a reclining position on a comfortable chair opposite the large dresser that had been set up with all the essential make-up items that a bride-to-be would require, as well as an array of devices that would satisfy the omega’s sexual needs until the mating. 

Derek ignored it all for the moment, focused solely on the way the omega was responding to the ministrations of the man gently pleasuring his hole with his mouth. Derek knew that the best way to keep an omega satisfied was to keep his cunt wet and aroused, and he’d scheduled several hours of pussy-eating every day, assigning six of his best-trained men to the task to ensure that his fiancée would be well-pleasured while Derek was otherwise occupied. Unable to deny himself any longer, he unbuttoned his trousers and took himself in hand as he watched the erotic display in front of him. His wife—god, he already thought of the gorgeous, writhing creature in front of him as his wife—was letting out soft, almost reluctant-sounding chirps of pleasure through the penis-shaped rubber gag tied into her mouth, her head rolling from side to side in desperate lust. When pleasuring himself, Derek could only use the female pronoun as he fantasized about his mate. She was made for this, meant to be fucked and knotted and pleasured into sexual oblivion. There was no need to fantasize now, because the gifts of her exquisite body were on lewd display for Derek’s hungry eyes. Her arms were bound behind her with soft ropes, her legs tied open so that her cunt was completely exposed. The man pleasuring her was holding her ass cheeks apart with his large, callused hands, his tongue licking gently but insistently at the slick, glistening hole. Stiles’s whimpers formed a near-constant moan, body moving in a slow, erotic struggle against its ropes, cunt lips twitching and clenching against the tongue that moved between them with slow, obscene grace.

There was no way Derek was going to last. The sounds the omega made under the gag had already had him rock-hard the moment he’d entered the room. Stroking his cock as slowly as possible, trying to draw out his excitement, he walked up to the chair and curled his fingers into his bride’s soft, recently-shampooed hair, angling her head so she could see how aroused he was. 

“Enjoying yourself, my sweet?” He bent to lick around the gag in her mouth. Her lips had been lightly painted with pink gloss, and he traced their plump softness with the tip of his tongue, groaning with barely-restrained need, fisting his cock harder as he kissed his way up her face, tongue flicking against his mate’s nostrils and eyelids. 

“God, what you do to me.” Stepping behind her, Derek let his cock slide into her soft hair. It wasn’t long enough yet for it to cover his cock completely, but it had grown enough for him to sink his fingers into it and grasp two handfuls as he moved her head back and forth, sighing with pleasure at the feel of her silken hair caressing his cock. His knot was forming rapidly, swelling large and needy against her head. 

“Look in the mirror, baby slut,” Derek chided gently, patting the side of her face as she closed her eyes, moaning incessantly in delicious torment. He was close, so close, and he wanted her to see. When she refused to obey, he opened her eyelids with his fingertips, using gentle but necessary force, pushing her head up using his thrusting cock until she was compelled to look into the wall-sized mirror in front of her. Keeping her eyes held open, he began thrusting against her hair with faster strokes, knot rubbing into her hair and the rest of his long, thick cock rubbing against her face, dripping head bumping against her nose.

“Tongue-fuck her. As deep as you can go.” He groaned out the order, barely able to hear himself over his own panting breaths and her gagged mewls. The man between the omega’s legs complied immediately, tongue slipping more deeply into the omega’s tight, fucked-open hole, his nose and chin covered with her slick juices. He began stabbing his tongue into the omega’s hole, using the gentle force that Derek had trained his men to use, making small, almost hungry sounds against the spasming cunt as he thrust his tongue in and out, slowly but forcefully. The sight of the gentle torture was entirely visible to Derek and his mate in the mirror, and Derek could hold back no longer. He ejaculated with a deep, guttural moan over his wife’s face, his gaze fixed on her lovely ass-lips clenching around the tongue that was still fucking leisurely between them. They weren’t knotted, but it still took several minutes for Derek to finish coming over the omega’s face and hair. Pearly strings of her alpha’s come trickled down her cheeks and chin and pooled in the hollow of her throat, tiny rivulets finding their way to her oiled tits and slipping down her chest. Fuck, she was exquisite like this, bound and gagged and writhing prettily on a man's thick tongue, dressed in her sexy little scraps of lace and drenched in her alpha's come.

Stepping back around the chair, Derek thrust his softening cock gently over her come-covered mouth, giving her a taste of his flesh. “You did well, my bitch. Very well indeed.” He touched his omega’s chastised clit with his wet fingers, feeling the captive organ throb with need beneath his touch. Unable to resist a taste, he bent and suckled the restrained nub of flesh softly between his lips, feeling the omega’s body—still being tongue-fucked—quiver with need. “Soon, baby girl,” he said, straightening up and tucking his spent cock back into his trousers. “I’ll have you milked soon.”


	5. Chapter 5

Derek whistled softly to himself as he got ready for bed. He’d decided to sleep in Stiles’s chambers tonight, reluctant to leave the boy alone during his first night at the manor.

He undressed completely, tossing his clothes over a chair and sliding into bed behind Stiles. While it was undeniably arousing to watch his men pleasure the boy, Derek needed some time alone with him. Stiles lay on his side, his arms and legs strapped together with broad, soft belts. He still wore his negligee and his rubber gag, and a soft collar around his throat was attached to the headboard, ensuring that he couldn’t lift his head more than a few inches. Derek cupped his naked ass gently, kissing behind his ear. “Miss me, darlin’?”

Stiles let out a muffled moan, trying to twist his head around, but stopped by the chain. Chuckling, Derek licked into his ear as he played with the fat plug wedged into Stiles’s hole. His hand was wet in seconds. 

“Mmm,” he murmured, propping himself on an elbow to kiss his way down Stiles’s face and neck, stopping at his nipple to tongue the pierced bud. Releasing the plug, he slid his hand over Stiles’s waist and cupped his genitals, rubbing his wetness all over them. The boy’s captive cock twitched at Derek’s touch, and he pushed his cock into the crack of Stiles’s ass, beginning to rock against the plug. The omega wriggled in his bonds like a fish on a hook, letting out breathy moans as Derek rubbed at his soft nub of a cock like he was pleasuring a girl’s clit. Continuing to finger Stiles’s cock with the pad of his thumb, Derek cupped the omega’s bound balls in his palm, squeezing them lightly.

“Bet these are full of come,” he murmured, biting down on Stiles’s nipple as he continued to hump against the boy’s naked bottom. “Just like a sow’s udders. Maybe I’ll take you out to the barns tomorrow, let some piglets suckle on your teat”—he squeezed the omega’s little cock, just to make it clear what he meant—“and get all that milk out, suck you nice and dry. Would you like that, little sow? To play wife to the boar pigs and mother to all those piglets? Tie you to a breeding bench, let your wet little teat and udders dangle over a box of hungry piglets just waiting to suckle.”

The omega was thrashing frantically in his arms, letting out little high-pitched whines. “Oinking like a slutty little sow,” Derek laughed. “But you need to stay still for your master, you fucking _pig_.” He brought his hand down hard against the omega’s rump, leaving a bright red handprint that stood out starkly against Stiles’s pale skin and the lacy white nightie he was wearing. Stiles squealed and writhed, and Derek spanked him again, just to hear that sound. “You sound like a sow in heat, you cunt.”

As delightful as the game was, Derek couldn’t wait any longer. Shoving Stiles on to his stomach, he mounted the omega like they were going to knot, fucking his cock hard and fast against the soaking wet crack of Stiles’s ass. He forced both his hands under Stiles as he humped the boy hard, grabbing a tit with one hand and squeezing the boy’s cock and balls with the other. He made sure that he hit the base of the anal plug with every brutal thrust, letting his slut enjoy the pseudo-rape. As he drove himself closer to climax, he treated the boy’s bare neck and shoulders to urgent, feral bites, growling out more fantasies about what he’d let the pigs in the barn do to their sow.

“Make it part of your wifely duties to offer your cunt to the pigs every day,” he gasped, “while the young ones suckle your teat. Your fucking udders. Tie you down so you can’t even wriggle, your filthy wet cunt pushed up for the pigs to lick and fuck. Spray your dripping hole with the juices from sows in heat, make you irresistible to the boars. God, I want to hear the moans from your gagged mouth while they breed you. Leave you with them all day and night, let them take turns with you till your belly’s so fucking full of pig come that you look pregnant. Well bred and knocked up.”

The omega’s frantic writhing was perfect, and coupled with Derek’s urgent thrusts against his ass, it wasn’t long before he was coming hard, his cock spasming against the plug, pushing it deeper than ever into the boy’s rectum as he wildly humped his way through his orgasm, groaning in pleasure. He grabbed the boy’s collar and twisted it tighter as he came, cutting off his breath, ensuring that the boy struggled even more desperately. Fuck, he was perfect.

Spent, he rolled over and gave the boy’s wet bottom a last hard slap. “That was great, baby. We should do this every night till we’re married and I can take you properly. What d’you say? Something to take the edge off, hmmm?” The omega moaned piteously, still struggling weakly against his tight bindings, and Derek let the sound of his sweet moans lull him into sleep.


	6. interlude

They first met over a year ago, in the kind of place that Derek despised: a dimly-lit, smoke-filled club that catered to the needs of alphas and omegas who wanted a quick fuck without the hassles of permanent mating. Large, obscenely garish chandeliers dangled from the ceiling, light spreading through cut glass to give the large room an air of opulence. 

Derek smelled the sweet, heady fragrance of ripe omega even before he stepped into the club. This was why he came here, despite his misgivings. One whiff of the place, and he felt an ease settling into his body, the kind of satisfaction that could only come from knowing that one’s needs were soon to be fulfilled. He never fucked the same omega twice, even though there were more than a few regulars. 

Later, he didn’t know what drew him to the lone omega sitting at the bar. He was good-looking, but so were a dozen others in the club, and Derek had long since learned to recognize that anyone could look good enough to fuck in an environment that was heavy with the smell of heat and slick and arousal.

Taking the empty stool next to the boy, he gave the bartender a perfunctory smile. His usual order was quickly placed on the counter in front of him, and he dismissed the bartender with a nod of thanks, turning his attention to the boy next to him.

“What?” the omega asked irritably, throwing him a half-glance.

Derek suddenly realized what it was about the boy that seemed so muted, despite the fact that his features were attractive enough. “You’re on suppressants.”

“Give the man a gold star.” The boy threw back his head and downed the rest of his drink in one graceful move. He tapped the rim of his glass to signal that he wanted another.

“Why would you be here, if you aren’t looking for a knot?”

“Are you always this inquisitive?”

Derek shrugged. “Not really, no.”

“Dysfunctional, then?” The boy smirked.

Derek smiled. “Hardly.”

“Then go find a hole to fuck, and leave me alone.”

Derek squeezed his glass between his hands, willing himself to keep his temper in check. He’d never been one to hold back his anger, but an outspoken omega was a rare thing, especially in a place such as this, where even the more recalcitrant omegas suppressed their true natures in hopes of getting what they wanted. “Not everyone is here for a fuck, as you yourself have indicated, omega.” He couldn’t help placing a slight emphasis on the last word, curious, despite himself, to see how the boy would react.

The boy’s face went blank. “Don’t call me that.”

“Give me a name, then.”

“Stiles,” the boy said shortly, almost biting the word out.

Derek smiled. “That wasn’t so hard, was it?”

“I’m not here to be patronized, Mr Tall-Obnoxious-and-Alpha.” 

“It’s Derek,” Derek said, amused. He held out his hand, half-turning in his seat to face the boy. “Derek Hale.”

He was surprised when Stiles took his hand. He was raising his eyebrows again, smirk gracing his face. His grip was firm. “That almost sounds like a respectable name.”

“Oh, I’m very respectable.” Derek took another sip of his drink, enjoying their verbal give and take more than he was inclined to admit. 

Stiles snorted into his drink, reclaiming his hand. “Somehow, I doubt that.”

“If I weren’t, I’d be dragging you into one of the back rooms by the scruff of your neck right now.”

Stiles’s eyes flashed, and not with lust. “I’d like to see you try.”

“Oh, you will.” Derek stood up and dropped a few bills on the counter, enough to cover both their orders plus a generous tip. “But not tonight.” He took out one of his business cards and slid it across to Stiles, and the boy made a show of tearing it into two and dropping the pieces into Derek’s glass.

Derek threw back his head and laughed. This was going to be fun.


	7. Chapter 7

Derek woke with a start, disoriented for a moment before he remembered that he was in the renovated basement. The clock on the wall showed that it was just after midnight.

He turned his head on the pillow to look at the restrained figure beside him. Stiles was awake, lying on his back, his gaze focused on the ceiling. 

Reaching over, Derek unfastened the gag from his mouth and tossed it aside. He sat up and reached for the glass of water on the night table. Stiles said nothing as Derek slid a hand under his neck to lift his head up, but sipped from the glass.

“More?” Derek asked after a moment. 

Stiles shook his head. He didn’t meet Derek’s eyes, and Derek watched him for a minute. He’d wondered, maybe even hoped, that they might have a bit of a conversation, but if Stiles wasn’t inclined that way, there were other things they could continue to do.

Moving lower down the bed, he lightly nuzzled the boy’s restrained balls. They were tight and full, perfectly hairless in accordance with Derek’s instructions. Thin cords of soft white silk kept them bound separate from each other, and were also wound around the base of his cock. They weren’t tight enough to stop his blood from circulating, or to keep his cock from hardening, but a silver chastity tube took care of that. The soft head of the omega’s cock peeked out from the end of the chastity device, small and wet like an aroused clitoris. Derek flicked his tongue out and tasted it, pleased by Stiles’s involuntary moan, and sucked it gently into his mouth.

“Fuck,” Stiles gasped. “You fucking asshole.”

Derek let out a laugh, slipping a hand beneath the boy and pressing his palm against the base of the plug that was filling him up. “Need something, darling?”

“Go to hell,” Stiles said through gritted teeth.

“I was going to release this pretty little bitch stick you have”—Derek tapped his finger against the silver tube, flicking the helpless little cock from side to side—“but if you’re going to be such an ungrateful little brat, maybe I’ll just milk you without taking this off. You want that?”

Stiles didn’t respond for a minute. Derek waited, patient, playing lightly with the boy’s sex. “No,” Stiles said finally, the word barely a syllable, a bitten-off sound.

Derek smiled. “Not bad, but you have to tell me what you want.” When Stiles didn’t respond, Derek raised his hand and brought it down in a brief, stinging slap against his balls. Stiles let out a shout of protest. 

“Answer me when I give you a fucking order.” Derek slapped the boy’s balls again, and then once more for good measure.

“Let me come,” Stiles said through clenched teeth. “Please, let me come.”

“That wasn’t so hard, was it?” Flicking the chastity device open, Derek reached for a small bottle of oil from the table and let a few drops fall on Stiles’s cock. He began massaging it slowly, feeling his own cock twitch in response as the boy’s length swelled and hardened in his hand. 

Stiles’s hips began to move, thrusting up into Derek’s hand. Derek tightened his hand around the hard shaft, tugging the neck of the negligee further down Stiles’s chest so that his nipples were exposed. Bending his head, he took one into his mouth, sucking lightly on it and worrying the small gold ring with his teeth. Stiles moaned, pushing his chest up for more.

“That’s it, bitch. Show me what a slut you are for this. Work those hips for me like you have a real cock fucking your wet little hole.” Derek laid bites onto and around both of the boy’s tits, leaving marks all over his chest. Stiles’s hips were thrusting frantically up and down, and the sight of his bound, writhing form was delicious. He’d been stimulated for so long without being given any release that his need to come seemed to have overtaken everything else, and he babbled helplessly as he chased his orgasm. Derek bit down hard on his nipple as he came and milked the boy’s cock through it, tightening his oily fingers and working the boy hard and fast.

Derek played with the boy’s cock until it finally began to soften, and Stiles started squirming with oversensitivity. He thrust his wet fingers into Stiles’s slack, open mouth, and Stiles licked weakly at them. “Good girl,” Derek murmured, moving his fingers around inside the omega’s soft, wet mouth. “Lick your bitch juices off. Get them nice and clean.” Stiles didn’t exactly obey, but Derek rubbed his fingers over his tongue until he was satisfied that most of the omega’s come had been fed into his mouth.

Derek slid out of bed. He’d spend the rest of the night in his own room, since he’d already spent an inappropriate amount of time in the chambers of his bride-to-be. “Get some rest,” he said, pushing the gag back into Stiles’s mouth. “We have a long and interesting day tomorrow.”


	8. Chapter 8

Derek was up early on the morning of the second day of his arrangement with Stiles, wanting to get in a quick ‘good morning’ before breakfast. He slipped into bed behind Stiles, pleased to see that the boy was sleeping soundly. 

The omega’s cock was soft against his thigh, and Derek slipped it back into its silver chastity tube, tightening the thin silk strap around his balls, separating them until they stood out in their bindings, full and taut. Stiles stirred under his touch, letting out a soft whimper. He was still asleep.

Derek pressed close behind him, licking behind his ear as he continued to lightly fondle the boy’s trapped genitals. “Morning, slut.”

Stiles huffed out a breath, his eyelids flickering open. Derek lifted his head and closed his lips over the boy’s nose, tonguing his nostrils thoroughly. Fuck, the little bitch tasted good everywhere. Stiles spluttered under him, trying to twist his head away from the onslaught, and Derek chuckled. “Hate that, don’t you?” He did it again, inserting the tip of his tongue into each nostril in turn, wetting the inside of it while he squeezed on the boy’s bound sac.

“I’m going to be working for a couple of hours,” Derek murmured, leaving a trail of bites down the omega’s throat, “while you get ready for our ride. We’ll leave around noon. You like horses, don’t you?”

Stiles growled under his gag, and Derek laughed. “Don’t worry, I won’t let the horses fuck you. Although it’s a tempting thought, the idea of watching you get bred by my prize stallions like a mare in heat.” He felt the boy’s cock twitch under his palm, and squeezed it lightly. “Maybe someday, hmm?”

Cupping the boy’s chin, Derek turned his head around to face the mannequin that had been placed in front of the wall-sized mirror. “Like your outfit for today?”

For the most part, the dress was befitting of any genteel young lady. Its petticoats were thick and layered so that the long, full skirt would flare out prettily. Its bodice was a soft beige, complementing the darker burgundy of the skirt and sleeves. Soft silk ribbons, matching the dark red of the dress, were threaded through the front of the bodice, and Derek groaned with arousal at the thought of tightening them over the omega’s chest. He pushed his clothed cock against the omega’s naked behind, rubbing against his plugged hole, while he murmured filth into the boy’s ear as he forced him to keep gazing at the dress.

Derek’s two favorite parts of the dress were its back and sides. The sides were held together with laces that could be loosened for easy access while riding, and the back was a thing of beauty. “Too bad you can’t see it while you’re in this position,” he said into the boy’s ear, and licked into the shell. Stiles wriggled against him, pushing back against his cock. His hole was growing wet again, his slick leaking around the wooden plug and into the crotch of Derek’s trousers. “It’s got a lovely little opening at the back. Heart-shaped, like your ripe little bottom.” He nipped the lobe of Stiles’s ear, reveling in the moan that Stiles let out. “I’ll let your attendees get you ready for the ride. See you soon, bitch.”


	9. Interlude II

**Notes for the Chapter:**

> No more porn yet, my lovelies, but have some more backstory.

“I thought you tore up my business card.” Derek slid into the seat opposite Stiles’s, gracing the kid with a smile.

Stiles shrugged. “I did.”

“And drowned the pieces in your glass of—what was it again?”

Stiles didn’t answer, but Derek signaled for a waiter. “A bottle of Chardonnay, please. Do you have the ’78? Wonderful, thanks.”

“Why ask if you already knew?” Stiles lifted an eyebrow.

“No matter.” Truth be told, Derek liked his partners a little more assertive than Stiles was apparently willing to be, but the fact that the boy had called his assistant and set up a meeting was promising. Actions could indeed speak louder than words, on occasion. “I believe you have a proposal for me.”

Stiles let out a short laugh. “More like a proposition, really.”

Derek’s lips quirked. “Go on.”

Stiles took a sip of his wine. “Three days. I’ll give you three days.”

“Three days of what?”

“Three days of you playing alpha to my helpless little omega.”

“What makes you think I like my omegas helpless?”

“Maybe you do. Maybe you don’t.” 

“Ah.” Derek watched as the boy slipped a piece of cheese into his mouth. “Wish fulfillment? Is that what you want?”

“Why not?” Stiles swallowed his cheese, his eyes hooded in the dim lighting of the restaurant. “You get to knot me, I get what I want, everyone goes home happy.”

“What makes you think I want to knot you?”

Stiles laughed. “I can smell how bad you want me, mister.”

Derek looked around the room for a minute. To a casual observer, they were just two people discussing a business deal. Possibly friends, even. 

He turned his gaze back on Stiles. “How much?”

The omega gave him a measured look. He’d been expecting the question. “I’m not a fucking whore,” he said, keeping his tone conversational. 

“You don’t want anything in return?”

“Haven’t you been listening? I said we both get what we want.”

“No holds barred?”

“None.” Stiles drained the last of his wine. “Don’t mark me permanently, and don’t think you can whore me around. Only you get to knot me.”

“That’s it? Those are your terms?”

“Pretty much, yeah.”

“What if I want more than three days? Or less?”

“You won’t want less.” 

“Are you that confident? Or just arrogant?”

“Neither.” Stiles waved a hand between them. “Don’t tell me you don’t sense it.”

Derek knew exactly what he meant. He could feel the chemistry between them, had felt it the moment he set eyes on the boy, even though he was on suppressants. They’d be good together, physically if in no other way. Their pheromones had made that abundantly clear.

“Would you care to put it to the test?”

Stiles gave him a sudden grin, and Derek blinked with surprise. The kid really was quite charming. “Didn’t think you’re the sort who’s okay with making out in public.”

“I have a car. Presumably, you need a ride home.” Derek met his eyes, unabashed, and Stiles held his gaze for a moment before he nodded.

 

*

 

They spent most of the ride in silence, sitting across from each other at the back of Derek’s limousine, sipping from the flutes of champagne Derek had poured them both. The address Stiles had given the chauffeur wasn’t exactly the shabbiest part of town, but it wasn’t the Ritz, either.

The car pulled to a stop, and Derek glanced at the apartment building. Fairly nondescript, with peeling paint and the odd broken window.

He turned back to Stiles and tilted his head, indicating the seat beside him. Stiles moved over to sit next to him. “What, no disparaging remarks about where I live?”

“Where you live is none of my concern.” Derek cupped his hand behind the omega’s neck and pulled him in for a kiss.

Stiles’s mouth opened under his immediately. Derek had time to register the thought that he _really_ liked how there was nothing remotely tentative about the boy’s approach before his senses were entirely ensnared by the taste of the eager young mouth against his. Stiles fisted his hands in the front of Derek’s silk shirt and all but climbed into his lap, giving as good as he got, letting out a small, restrained moan around Derek’s exploring tongue. 

The tension between them sparked like electricity, and Derek cupped the omega’s ass and squeezed, pulling his body closer. “A week from now,” he said when they parted for air. He had all the proof he needed.

“Sounds good,” Stiles said, sounding only a little breathless.

They clinked glasses and then Stiles was gone, slipping noiselessly from the car and into the darkness of the street.


	10. Chapter 10

Derek finished the last of his paperwork and wiped the nib of his fountain pen carefully with a rag before setting it back in its holder. It was just past noon; plenty of time to take a horse ride before lunch. He’d ordered a picnic, so they could eat leisurely before returning to the house.

He took a quick shower before going out to the stables. His cock hardened under the warm spray of water and he stroked it leisurely, tempted to bring himself to completion, but stopping himself. His boy would appreciate his come far more than the drain would.

Denying himself release brought its own form of pleasure. Before dressing in his riding outfit, he snapped a close-fitting ring around the base of his cock, his body already thrumming in anticipation of the afternoon’s activities.

His riding boots had been shined to perfection, and the rest of his outfit was dark brown, matching his boots. He’d picked out that one because the color would go well with the rich burgundy of Stiles’s dress. 

Picking up his riding crop, he stepped out of the room and into the large courtyard, where his favorite stallion was already awaiting him. He stroked Thunder’s flank and checked his saddlebags to ensure that everything they needed had been stored in them.

Thunder was large, easily able to carry two riders. Today, he was wearing a specially made double saddle. On to the seat in front was buckled a broad strap, attached to which was a thick wooden phallus, already oiled and glistening and ready for its rider.

His men had ensured that he wouldn’t be kept waiting; already he could hear the sound of muffled moans. He turned around, shading his eyes against the noon sun, to watch appreciatively as Stiles was brought down the steps.

Two of Derek’s men were carrying the wriggling omega, who looked particularly fetching in his wine-red dress. He wore soft, elbow-length gloves and satin slippers that matched his dress, and a pretty bonnet was on his head, to shield him from the sun. It would come off soon enough when they started on their ride along the shaded path; Derek wanted to watch every single expression that graced the omega’s face. 

Stiles was, of course, bound thoroughly for his ride. Derek had chosen black ropes for today, and the boy’s arms were tied at wrists and elbows behind his back, his legs fastened together at the thighs, knees, and ankles. A black muzzle-style gag completed his outfit. 

Stiles was set down beside Derek, who ran a fingertip softly down the omega’s cheek. “Exquisite,” he murmured, placing a light kiss on top of the gag. “Turn around, darling. Let’s have a good look at you.”

He grinned as Stiles inched himself around in a half-circle, wobbling on his bound legs. 

The omega’s ass looked every bit as delicious as Derek had imagined it would. The thick skirts of the dress parted above and below Stiles’s bottom, framing it in a perfect heart-shape. Wrapping an arm around the boy’s waist, Derek pulled him closer. “Bend over, sweetheart. Let me make sure you’re ready for your ride.” 

He parted the boy’s luscious cheeks with his free hand, pleased to see the tell-tale glistening on the omega’s tender flesh. “Mm,” he said appreciatively, squeezing Stiles’s left cheek. “You look great, sweetheart. But let’s make sure you’re good and wet, hmm?” Letting go of the boy, he pushed him lightly toward the waiting men. “Do your job, boys.”

The men, Havisham and Doyle, caught Stiles easily as he stumbled toward them. Doyle, the man who’d enthusiastically eaten the omega’s ass the previous day, gripped the boy in his arms and lifted him over one of his shoulders, holding his ass cheeks apart, while Havisham stepped up to bury his face in the omega’s ass. Muffled whimpers and noisy slurping soon filled the air, Stiles wriggling over his captor’s shoulders, bound feet twisting cutely in their delicate slippers as his hole was ravished by Havisham’s thick tongue. The man was usually unshaven, and Derek smiled at the thought of how his stubble must feel on Stiles’s sensitive skin.

Derek stepped around Doyle’s broad form. Stiles’s torso dangled helpless along the man’s back. Derek cupped the whimpering omega’s chin, forcing his head up. “Feel good, darling?”

The look Stiles gave him was murderous, but his eyes were blown with lust. Derek chuckled, slapping his face lightly. “All right, boys. Get the lady up into her seat.”

He watched with great enjoyment as Doyle lifted Stiles and lowered him slowly over the saddle, the shining dildo disappearing inch by inch into Stiles’s clutching hole. 

“Good girls ride side-saddle,” Derek reminded Stiles, patting his ass while Havisham tightened a thick strap over Stiles’s thighs, ensuring that the phallus would remain deeply lodged inside him during the ride. Stiles moaned as the strap was pulled taut, squirming in his seat.

Derek swung up into his own seat, taking the reins. The omega was snug in his arms, smelling divinely of light perfume, fragrant oil, and his own rich alluring scent. “Ready, baby?” Derek murmured, brushing his lips against the boy’s ear. Stiles didn’t deign to answer, and Derek laughed and clicked his tongue, tugging lightly on Thunder’s reins. 

They set off at a light canter. Thunder was well-trained, attuned to sensing what Derek wanted, and the first few minutes of the ride were slow and pleasurable. Derek held the reins lightly in one hand and explored the omega’s body with the other, groping and squeezing every once in a while, just to startle a delicious whimper from the boy’s well-gagged mouth.

“Enjoying this?” he asked, reaching for the top button on the high collar of the dress. Slowly, he slid the small pearls from their clasps, taking the time to savor each inch of the long column of Stiles’s throat as it was bared to Derek’s gaze. “I think we could go a little faster. What do you say, bitch?”

Slipping a hand inside Stiles’s dress, Derek caught a nipple-ring and tugged on it as he pulled at the reins to make Thunder canter faster. Stiles moaned at the sudden increase in pace, his torso twisting in Derek’s arms as he tried to pull away from Derek’s fingers.

“Good?” Derek reached for the strap over Stiles’s thighs, loosening it just a little. “Let’s give you a bit of room to bounce on that cock, shall we?” He licked up the side of Stiles’s neck and caught the reins with both hands. “Giddy up, Thunder!”

Thunder broke into a gallop, his chestnut mane blown back in the breeze, thoroughly enjoying himself. 

Sandwiched between Derek’s arms, Stiles was positively squealing now, his pretty behind bouncing up and down as much as his bondage would allow. “That’s it,” Derek encouraged, tugging the bonnet off Stiles’s head so that he could bite and suck on the boy’s earlobe. “That’s it, slut. Fuck yourself on that cock. Up and down, there you go. Good girl.”

He couldn’t really tell if Stiles was actually making the effort to fuck himself actively on the phallus, but the pace of Thunder’s galloping was enough to ensure that the boy was rocked up and down on his saddle, every movement punching the most delicious-sounding moans out of the helpless omega. 

“Wriggle, bitch.” Derek tugged the riding crop free from its place on his belt and struck the boy’s rump with a satisfying crack. “Fuck that thing like you mean it.” 

“Mmmmmph!” Stiles was obviously trying to say something in protest, but the sounds he was making were too arousing to ungag him just yet. Derek struck him with the crop again. “Like you _mean_ it, slut. Move that fucking ass.” Stiles huffed through the gag, his chest heaving with the strain, and Derek slapped his ass with the crop again. 

After a few minutes of listening to Stiles’s frenzied moans, he slowed Thunder to a canter, reaching inside Stiles’s open dress to fondle his nipples again. “There you go, whore. Now you get to do the actual work. Wouldn’t want to tire poor Thunder out.” He tapped Stiles’s bottom with the crop. “Keep humping, slut, or it’s the gallop again.”

Now to exploit the true beauty of Stiles’s outfit. Derek reached between them to loosen a couple of the ribbons along the side, and then reached around the writhing body to do the same on the other side. The dress parted easily, designed for easy access, exposing the omega’s cock and balls to the afternoon air. 

Derek hummed with appreciation at the sight of the boy’s cock. Snug in its silver chastity tube, it was beaded with wetness. Derek cupped the soft, warm flesh in his palm, easily able to gather the bound cock and balls in his hand and squeeze them. “Looks like your little clit is enjoying the horse ride,” he teased, rolling the slick, trapped genitals in his palm. Stiles tried to push up into the touch, still humping his dildo with urgent movements, rocking up and down, desperate for release, his dripping ass squelching loudly with every frantic thrust.

“Harder,” Derek ordered, releasing the boy’s cock and returning to molesting his tits. “Faster, whore. Work that cunt. Isn’t that cock enough for it? Hmm?” He bit into Stiles’s earlobe again, and ran his tongue along the shell of the boy’s ear. “You want Thunder’s cock instead? His giant stallion cock? Maybe you’d rather be tied beneath him instead, getting fucked by his thick rod while he gallops? Your pretty little dress fluttering around you while he breeds you like a fucking mare in heat?”

Stiles’s eyes were squeezed shut, and Derek knew he was drinking in all the filthy words that Derek was throwing at him, whimpering his responses while he obediently fucked himself on his dildo, mindlessly chasing a release that he wouldn’t be given for a while. Derek’s own cock was painfully hard in the ring that was keeping his knot from forming, and he knew they’d need to stop soon.

He guided Thunder to a stop when they reached the clearing he’d had in mind. He slid off the horse and got Thunder’s favorite lunch out of one of the saddlebags—apples and carrots. 

Stiles was still rocking up and down, oblivious to their surroundings. Chuckling, Derek left him to it for a while, getting a blanket and their food out and setting it up on a soft patch of grass. He returned to Stiles and tapped him on the face. “Easy, bitch. Time for a break.” Stiles opened his eyes, still squirming, letting out a tiny mewl. Derek unbuckled the strap around his thighs and tugged him off the horse into his arms, carrying him bridal-style to the blanket and setting him down with his back against a tree. 

He undid the gag and immediately forced Stiles’s face up and into a hungry kiss, delving deep into the omega’s mouth. Stiles tried to turn his face away but Derek gripped his jaw tightly. “Keep that fucking hole open, or I’ll gag you again while I eat.”

Stiles’s eyes, still glazed with arousal, resignedly met Derek’s. He parted his lips, remaining pliant in Derek’s arms as Derek fucked the boy’s open mouth with his tongue.

“Delicious,” Derek said as he finally pulled away. “Lie down. On your front.” Grabbing Stiles’s bound arms, he forced the omega face down on the blanket and parted the boy’s slippery ass cheeks to admire his twitching hole. “So tempting,” he said, running a finger along Stiles’s crack before slipping it deep into his hole, easily finding his prostate. 

“Please,” Stiles gasped, his wet hole clenching and unclenching around Derek’s finger. “Please, fuck. Fuck. Please let me come.”

Derek smiled, bending his head to lick around his finger, greedily lapping up the omega’s slick. “So fucking pretty,” he murmured against the boy’s flushed skin. “Look how wet you get from all the things I do to you.”

“Bastard,” Stiles said through gritted teeth, his hips moving up to chase Derek’s finger when he withdrew it, wiping his hand on Stiles’s skirt.

“Apologize for that, or you’ll remain tied up.” Derek smacked the boy’s ass, making him gasp.

“Go fuck yourself,” Stiles snarled, trying to twist away as Derek slapped him again.

“I’d much rather fuck you,” Derek said, amused.

“You won’t,” Stiles scoffed, and Derek marveled, not for the first time, at the omega’s resilience. “Not before your ridiculous ceremony.”

“You’re right,” Derek said with a smile, turning Stiles over on to his side. “I won’t knot you before tomorrow, but there’s a reason you have a mouth.”

He unbuttoned his riding breeches and released his erection, giving himself a few leisurely strokes. Stiles’s eyes followed the movement, and Derek slid his hand into the boy’s hair, rubbing his cock against Stiles’s face. “Like what you see?”

“Fuck you,” Stiles said, but there was no bite to it this time. Derek pushed the head of his cock against the boy’s lips, parting them easily. “Suck.”

He spent a thoroughly enjoyable few minutes fucking languidly in and out of the boy’s mouth. Stiles made a delicious picture, lying tied up on his side, his dress open at the bosom and between his legs, his bound genitals obscenely displayed, the very picture of a ravished captive. Keeping a tight grip on the omega’s hair to keep his head in place, Derek played with Stiles’s hole with his other hand, slipping two fingers in and out at a leisurely pace as he fucked his mouth. Stiles responded by wriggling in his ropes, pushing back against Derek’s thrusting fingers and greedily sucking on his cock, his hips thrusting into nothing as he tried desperately to give his cock some relief. 

Derek kept up the dirty talk for a while, enjoying the sight of Stiles getting increasingly desperate for release. When he couldn’t wait any longer, he pulled his cock ring off and groaned as his knot formed almost immediately, swelling against Stiles’s swollen lips. Gripping Stiles’s head with both hands, he shoved in hard, and came instantly at the sight of the boy’s cheeks swelling over his thick knot. Stiles sputtered and choked but Derek held him in place, grinding his hips against the boy’s face and forcing him to swallow as he came and came, his seed spilling out of the sides of the omega’s forced-open mouth and trickling down his cheeks.

Not for the first time, he wished he could tie an omega’s mouth to his knot the way he could tie an ass in place, but it was easy enough to create the illusion of it by gripping Stiles tightly, fingers over his throat. He reached out with his free hand to undo Stiles’s cock cage. “Turn over,” he said, slapping the boy’s ass. “Hump the ground.” 

Stiles obeyed instantly, wriggling over on to his front, his mouth still gagged with Derek’s swollen knot. Derek kept grinding his hips, reveling in the feel of Stiles’s hot, wet mouth around his cock as he spilled down the boy’s throat. He picked up the riding crop again and rained blows on Stiles’s upturned ass. “Hump, slut! Up and down like a good little whore. Moan around my knot. Show me how much you like this, you little bitch in heat.”

Held by his throat, Stiles gasped and moaned, making sputtering noises around the thick knot filling his mouth. The sight of his bound body writhing against the ground triggered another burst of pleasure from Derek, and he groaned aloud and moved his hips against the omega’s mouth, giving him the hard fucking they’d both been craving, keeping up his steady strikes on the boy’s wriggling ass. He knew the boy didn’t have limitless energy, and finally took pity on the creature and shoved the end of the crop into his hole, twisting it around. “Come for me, slut.”

Stiles let out a sob, his eyes streaming, his whole body going rigid as he orgasmed. Derek slumped back against the tree, letting the boy catch his breath while Derek’s cock gradually softened in his mouth, his ass still clutching at the crop embedded deep inside. Derek reached out and swatted playfully at the part of the crop that was sticking out, and Stiles muttered a weak, muffled protest around Derek’s cock. Chuckling, Derek lay back to relax. They’d ride back to the manor after lunch, and maybe he’d let Stiles ride bound face down in front of him this time, and enjoy the sight of his greedy little hole twitching around the crop all the way back. It would be the perfect end to a relaxing afternoon, exactly what they both needed before the ceremony the next day.


	11. Chapter 11

“Like it?” Derek leaned back against the doorframe, crossing his arms over his chest, watching Stiles. The boy was gazing critically at the outfit he was to wear for their ceremony the next day. Unbound and freshly showered, he wore one of Derek’s silk robes.

“It’ll do.” Stiles threw him a glance, and Derek grinned. 

“Come on. Surely this little offering deserves more praise than that.”

Stiles let out a non-committal sound, walking in a half-circle around the mannequin. 

“Why don’t you try it on?”

The boy snorted. “Isn’t it bad luck for you to see me in the dress before the wedding?”

Derek laughed out loud. “Only if it were a real wedding.” He watched as the boy laid a hand on the waist of the dress, moving it slowly upward and over the ribs of the corset. “It could be, you know.”

“You’re insane.” Stiles withdrew his hand and turned his back on the mannequin, reaching for his glass and swallowing the rest of his drink.

“Haven’t you enjoyed the last two days?”

“Not nearly enough to make me wish I could spend every day as a prisoner.”

“You wouldn’t be a prisoner.” Derek walked over to the dresser and refreshed their drinks. “You’d have wealth. Status. The freedom to do whatever you wished.”

Stiles accepted the glass Derek handed to him, acknowledging the gesture with a brief incline of his head. “And what would be in it for you?”

“Hasn’t our time together given you any indication of that?”

“It’s just sex, Derek. You’re drunk on it.”

“And you aren’t?”

“I’ll admit it’s been… interesting.”

“Interesting.” Derek lifted a hand and rested the back of it against the boy’s smooth cheek. “Is that all it’s been?” 

Stiles didn’t move away from the unsolicited touch, but didn’t respond either. Derek imagined there was a hint of a smile in his eyes.

“I must be losing my touch, then.” Derek leaned in for a brief kiss, brushing his lips against the boy’s. The caress was oddly intimate, and he moved away. “Strip.”

Stiles obeyed immediately, undoing the belt of his robe and letting it slide to the floor.

“This.” Derek sat down in an overstuffed chair. “This, you understand. Coarseness. Humiliation. Sexual transactions. But I make you an offer that anyone else in your place would not even think of refusing, and you scoff at it.”

“I’m not anyone else.”

“No. What you are is foolish beyond measure.”

“Why? Because I won’t be bought?”

Derek stared at him, incredulous. “Are you implying that you would rather marry for _love_? Is that the depth to which your foolishness descends?”

“Please. Now you’re just insulting me.” Stiles smiled humorlessly and took another swallow of his scotch.

Derek knew enough about his guest to identify when the boy was slamming up his walls. “Come here.”

Stiles glanced at the array of restraints set up along the wall. 

“Not this time.”

Stiles lifted an eyebrow, but set down his glass and walked up to Derek, who yanked the boy on to his lap. Twisting a hand up into Stiles’s hair, Derek tugged him down for a messy kiss, sliding his other hand around to probe at the boy’s hole. He wasn’t wet enough to be fucked yet.

“Show me how you get yourself off,” Derek said against Stiles’s mouth.

“Is this some new kink?” Eyes narrowing, Stiles braced himself with his hands on Derek’s shoulders, glaring down at him.

“Indulge me.”

“Like this?”

“Just like this.”

Stiles shrugged, taking himself in hand. “Suit yourself.”

“There’s one condition.”

“What’s that?” Stiles didn’t stop stroking himself. He was already completely hard.

“Whatever you’re thinking, say it aloud.”

“What if,” Stiles said, bracing himself with a hand on Derek’s chest, “I’m thinking about fucking you?”

There it was. “Tell me about it.”

“I’d slick you up with that oil you like to have your men rub all over me. Drip it into your hole, get you good and wet.”

Derek circled the boy’s hole with a fingertip, pleased to feel a hint of slick. He rubbed against it. “Go on.”

“Put you on your hands and knees. In front of the mirror, so you could see yourself get fucked like an omega.” Stiles arched his back as Derek’s finger slid inside him with little resistance, his eyes shut. His hand was working faster now, sliding easily over the pre-come he was leaking.

“And then?” Derek twisted his finger further inside, finding the boy’s prostate and massaging slowly.

“Fuck, Derek. That’s good.”

It was the second time that night that Stiles had said his name. Derek leaned in and bit his earlobe. “Keep talking.”

“I’d make you beg me to fuck you. I wouldn’t do it until you sounded like you really meant it.”

“I would mean it.” Derek thrust another finger inside him, and Stiles’s eyes flew open. He came with a gasp, almost as though his orgasm had been surprised out of him.

Derek withdrew his fingers and shoved them into Stiles’s mouth. “Clean up the mess you made.”

Stiles merely sat there for a moment, still straddling Derek’s thighs, his mouth slack around Derek’s fingers. “Hurry up, bitch.” Derek pushed his fingers in further, almost making the boy gag. “I haven’t all night.”


	12. Chapter 12

“Having fun?” Derek grinned, sipping at his wine as he nodded at Allison.

“Your parties will be the death of me, darling,” Allison said around a swirl of smoke, her elegant fingers wrapped around a long-stemmed cigarette holder. She wore a long, figure-hugging black gown, sequins shining softly at her neckline, her only jewelry the small, iridescent jewel at her throat.

Derek put a hand over his heart. “You refer to my wedding as a mere party? I am wounded, my lady.”

Allison laughed, a lazy hand reaching down to pet at her omega’s hair. “You are deliciously wicked, my lord. So where is your lovely bride?”

“You’ll see her soon enough at the ceremony,” Derek said with a wink, kissing Allison’s cheek before taking his leave and moving on to mingle with the other guests.

The ‘ceremony’ was to take place in the same hall, where a simulation of the traditional wedding altar had been set up at one end. The sight of the thing made Derek’s cock twitch with anticipation. Little more than a glorified breeding bench, the low white platform was equipped with restraints and a small bench for the omega to kneel on. Despite his eagerness to perform the pseudo-ritual he had planned for the night, Derek had to repress a shudder of revulsion at ‘real’ mating ceremonies that were performed in this vile, barbaric manner. His well-planned parties were for guests who, like him, lived under the veneer of civilized life while subverting the outdated norms of their society through such gatherings, to everyone’s mutual enjoyment. He glanced back to Allison Argent, grinning to see that her young man was now lapping enthusiastically at her toes, her short, shiny-red fingernails trailing over his naked, upturned ass.

His thoughts were interrupted as the traditional wedding song began to play, right on time. Taking his place beside the ceremonial bench, he turned to the door.

Stiles entered, moving slowly. It wasn’t difficult to see why: his legs were bound at the thighs and knees with white straps, forcing him to take small, halting steps on his high-heeled sandals. His legs were encased in thigh-high stockings, sheer and glistening. They were almost hidden beneath his floor-length white dress. Unlike traditional wedding dresses, this one was sleek rather than frilly, its skirt made of pale white silk that hugged Stiles’s hips and thighs. Slits along its sides enabled him to walk, baring his stockinged legs with every step. 

As he watched Stiles stagger down the aisle, gazed at with interest and admiration by the guests, Derek let his eyes drink their fill of his bound ‘bride’. He wasn’t sure which part of the outfit was his favorite. There was certainly something to be said for the exquisite corset that Stiles was wearing. Decorated with small, delicate pearls, it had a ribbed texture and hugged Stiles’s torso with unforgiving tightness, forcing him into an hourglass shape. Its tight neckline began just under his nipples, forcing them up and out in a parody of breasts. Little silver rings had been attached to his nipples, tugged down by a thin chain between them.

Perhaps Derek’s favorite part of the outfit was the small opening at Stiles’s crotch, through which his ‘clit’ protruded, soft and bare and begging to be played with. It was clamped with a small jeweled clip that was attached to the end of the chain dangling from his nipple rings, causing every movement he made to tug on his tits and clit. The deviously-designed chain was the reason that Stiles was letting out small, delicious-sounding whimpers with each step. The base of his cock and his balls were, of course, bound tightly in their chastity device under Stiles’s skirt, but were out of sight, leaving only the tip of his soft organ visible.

Stiles’s arms were, of course, in secure bondage. They were encased in a long, white, single glove, keeping them together behind his back, white straps lashed tightly over his elbows and wrists. A white ball-gag completed the ensemble, clearly visible under the translucent veil over the boy’s face. His exquisite backside was also showcased by his outfit: like the dress he’d worn the previous day, the skirt he was wearing had a heart-shaped opening for his bottom, but his ass was decorously hidden behind a veil similar to the one on his head.

The music ended as Stiles painstakingly reached Derek’s side, almost stumbling when he was beside the alpha. Derek steadied him with a hand on his arm, leaning in to kiss the omega’s cheek. “You look eminently fuckable, my sweet slut,” he murmured, sliding his hand under the veil covering Stiles’s ass and squeezing his left buttock. His hand came away wet and he wiped it on Stiles’s corset, smirking. 

Peter did the honors, reading out the archaic ceremonial vows with a barely-suppressed grin. He had, characteristically, altered the words so that they held a distinctly more sexual meaning. Derek rolled his eyes and repeated the words, vowing to “bind, gag and fuck his willing omega until the bitch blacked out from the intensity of her orgasms.”

“You may kiss your bride,” Peter said grandly at the end of the modified vows.

Not wasting a moment, Derek put his hands on Stiles’s shoulders and guided him to his knees at the bench, making him bend over so that his ass was high in the air. Lifting the veil over his naked rump, Derek parted the cheeks—already glistening with the omega’s desperate arousal—to allow his guests to see the treasure that lay within. In preparation for his husband’s kiss, Stiles’s hole had been dolled up with glistening red rouge. There were gasps of delighted approval from the gathered crowd, and Derek grinned and lowered his mouth to the red lips. Stiles was so wet that Derek’s tongue slid into him at once, and the bound omega began to writhe, moaning with barely restrained lust as Derek french-kissed his hole thoroughly. 

“Delicious,” he said as he withdrew, placing a last, light kiss on the tongued-open hole. He wiped his wet mouth on a handkerchief and gestured toward the captive bride. “Your turn, my lords and ladies.”

Stiles spent the next half-hour being rimmed by almost everyone present, handymen present by his side to refresh his rouge when it disappeared under the onslaught of kisses. Derek moved to the other side of the bench to lift the veil over his face at long last, running a fingertip over his parted lips. “Told you you’d enjoy the ceremony,” he said with a grin, reaching beneath Stiles to lightly finger his soft, protruding cock. “Your little clit’s enjoying all the attention your pussy’s getting, hmm?”

Stiles moaned his assent, pushing his cock into Derek’s hand, desperately seeking friction. Derek laughed, rubbing the straining little nub with slow, teasing strokes. “Not yet, bitch. Not until I’ve knotted you good and proper.”

After the guests had had their fill of tonguing Stiles’s pouting little hole, it was time for the ceremonial photographs. While his guests began to make good use of the sofas, cushions and divans scattered about the room, Derek scooped Stiles up in his arms and carried him over to the plush red couch at the other end of the room, and arranged him so that his hole was clearly visible. Freeing his erection, he pushed the head of his cock against Stiles’s dripping hole. The flash went off, the first picture capturing them as though at the start of the act of consummating their mating. The next photograph had Stiles straddling Derek, his back to Derek’s chest, Derek’s fingers twisting his nipple rings, his teeth sunk into Stiles’s neck in a mockery of the mating bite. 

After several more photographs, each capturing the two of them in a pose imitating a sexual position, Stiles was carried over to a chair to watch the evening’s festivities. Derek had designed the chair himself, expressly so that whoever was seated in it could be rimmed from beneath. He himself took a seat next to Stiles, playing with the squirming omega’s tits and cock as he was mercilessly rimmed from beneath by a string of Derek’s men. The tableau in front of them consisted of various sexual acts performed by the evening’s entertainers, containing everything that Derek enjoyed the most, from whipping and bondage to unrestrained fucking.

Throughout it all, Derek had to admit to himself that the most alluring sight of all was Stiles himself, writhing in all his bound glory as he was relentlessly stimulated from beneath. Derek kept up a stream of talk, languidly stroking his cock as he played with Stiles’s body.

“Wish that were you?” he murmured into Stiles’s ear, sucking the lobe into his mouth, as a bound male omega wearing flimsy harem pants was enthusiastically mounted and vigorously bred by a Great Dane. “A bitch in heat, getting a good breeding from a stud? Hmm?” Stiles was humping madly against his chair, fighting his restraints, little moans punched out from behind his gag. Derek leaned down and bit one of his nipples, licking around the silver ring. “Want your clit licked, slut?” He gestured for one of his men to come over, and soon Stiles was sobbing with need, thrashing around wildly in his chair as his ‘clit’ was licked and sucked with great enthusiasm. The oral onslaught on his hole continued from beneath.

Derek had planned to be a courteous host and remain with his guests until they were replete with pleasure and exhaustion, but he was only human, and there was only so much stimulation his senses could take before he gave in. The smell of sex and the moans of unrestrained arousal emanating from every corner of the room only served to fuel his need further. Ordering his men away, he lifted Stiles over his shoulder and carried him out of the room and down the corridor to their ceremonial bed.

He flung Stiles down, and the boy rolled over on to his back, looking up at Derek and moaning something unintelligible beneath his gag. Derek shoved him on to his front again, ripping the flimsy veil off his bottom and shoving himself into Stiles’s ass with one hard thrust. Stiles keened loudly and pushed back desperately for more.

Their first mating didn’t last long; they were both too desperate for it. “Stiles,” Derek gasped against the omega’s ear when he felt his knot beginning to swell. “Stiles—fuck, you little bitch, you little fucking cunt, I’m going to knot you, slut, gonna breed you so good, fuck.”

He collapsed forward over the omega, pinning the struggling body under his own, ignoring Stiles’s muffled protests for a few moments, letting waves of pleasure wash through him as he pumped his seed into the boy’s body. When Stiles started making choking sounds, Derek rolled his eyes and turned on to his side, dragging Stiles with him. “Such a drama queen,” he said into Stiles’s ear, still out of breath. 

Unbuckling the strap of the gag, he tugged it from Stiles’s mouth and set it aside. “So good, Stiles.” He buried his face in the boy’s sweaty neck, flicking out his tongue to taste the soft skin there. “So fucking good, baby.” He slid his arms around the omega’s restrained form, gently thumbing his sensitive nipples, and placed a light kiss on his bare shoulder. “Are you all right?”

“Are you going to let me come anytime soon?” Stiles inquired, his voice dripping with mock politeness, despite sounding a little hoarse. He’d been gagged for hours. 

Derek chuckled. “Patience, dearest. Good things come to those who wait.”

“Fuck you, ‘dearest’,” Stiles said, no bite in his tone. He wriggled back into Derek’s embrace, his hole clenching hotly around Derek’s knot. Derek groaned, reaching down to squeeze Stiles’s bound cock in retaliation.

“Fuck,” Stiles gasped. “You complete fucking asshole.”

“Language, darling.” Derek rocked his hips, deliberately stimulating Stiles’s prostate. The boy cried out in pleasure, his captive cock twitching helplessly in Derek’s hand.

“Fuck, Derek. Please. Please.”

“Please what, bitch?” Derek lifted his hand and brought it down with a sharp smack against Stiles’s bottom. 

“Let me come. Please let me come.”

Derek slapped his ass again. “That’s not how a good little slut asks to be allowed to come.”

“Please, Master.”

Derek pushed forward again, gasping in pleasure as Stiles’s hungry little hole made desperate sucking movements against his knot. “Be more specific, cunt.”

“Please let me come, Master.” Stiles was beginning to sound more than a little frantic now, no trace of sarcasm in his voice.

“Still not right, slut. A come-dump like you comes on its master’s cock. Its only pleasure is in its master’s pleasure.”

Stiles let out a sob of frustration, and Derek grinned into the omega’s damp hair. “Come on, come-dump. Tell me you want your sloppy little hole fucked. Tell me to fucking _rape_ it.” He clamped his hand over Stiles’s mouth, muffling whatever he was about to say, and rolled them over so that he was on top again. He began fucking Stiles again. His knot had gone down enough to allow him to move in and out of Stiles’s hole again, the boy’s ass already dripping with the come Derek had deposited in it.

“Tell me,” he snarled, putting on his alpha voice, taking his hand off Stiles’s mouth.

“Rape me,” Stiles gasped from beneath him, struggling for breath as Derek fucked mercilessly in and out of his ass. “Rape my hole, use me. Master.”

“That’s like a good slut.” Rising to his knees, Derek ripped the skirt apart with both his hands, reaching under Stiles to unclasp his chastity tube. The omega sobbed with relief as Derek grasped his cock and pumped it to hardness with a few quick strokes. Clamping his other hand over Stiles’s mouth again, he swiftly brought them both to orgasm.

He knotted Stiles twice more that night. First, he gagged Stiles again and made him ride his cock reverse-cowgirl style, making him face the mirror on the opposite wall and fuck himself up and down while Derek smacked his buttocks with a riding crop. Then, he untied Stiles and carried him to the bath, where they soaked in warm, fragrant water with Derek’s cock deeply embedded in Stiles’s ass. Stiles fell asleep on top of him, his breathing slow and even and content.

  
Epilogue

 

Sometimes, Derek likes to imagine what Stiles is doing at present. Sometimes he wonders if the boy ever found the envelope Derek had slipped into his coat pocket when he was leaving. Stiles hadn’t asked for a thing, but Derek hadn’t been able to let him go without any compensation for his time; the boy had certainly outdone himself. Stiles had left the morning after the faux-ceremony with a few parting words, none indicating that he would like to arrange another rendezvous.

Derek had let him go. The boy had his number.

It’s three months after the immensely satisfying tryst when the phone on his desk rings, startling Derek out of his thoughts. Putting down his pen, he picks it up and answers it with a curt hello.

The voice on the other end of the line brings a smile to his lips.

 

~end.


	13. Chapter 13

A brief prequel to the fic: http://archiveofourown.org/works/2019654.

Note: Link posted here for all 600+ of you who've subscribed to the fic. \o/ Thanks again! I won't post future links here; I've created a series for this 'verse, so those of you who wish to follow it may subscribe to the series instead. :)


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